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Thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols followed by the nucleophilic addition of water: metal-free and economical synthesis of arylcyclobutenals

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Abstract

Herein, we report an unprecedented thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols to form an aromatizing cyclobutachromene intermediate, followed by the nucleophilic addition of water to yield functionalized arylcyclobutenals. This reaction is atom- and pot-economical because all the atoms contained in the starting material are retained in the final product, no other reactants are required, and it proceeds in one-pot.

Graphical abstract: Thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols followed by the nucleophilic addition of water: metal-free and economical synthesis of arylcyclobutenals

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Article information


Submitted
07 Dec 2019
Accepted
09 Jan 2020
First published
13 Jan 2020

Green Chem., 2020, Advance Article
Article type
Paper

Thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols followed by the nucleophilic addition of water: metal-free and economical synthesis of arylcyclobutenals

S. Ohno, R. F. Avena, H. Aoyama, H. Fujioka and M. Arisawa, Green Chem., 2020, Advance Article , DOI: 10.1039/C9GC04184B

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